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O-1812

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Chemical compound Pharmaceutical compound
O-1812
Identifiers
IUPAC name
  • (5Z,8Z,11Z,14Z)-20-cyano-N--16,16-dimethylicosa-5,8,11,14-tetraenamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H42N2O2
Molar mass414.634 g·mol
3D model (JSmol)
SMILES
  • C(CO)NC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C(C)(C)CCCCC#N
InChI
  • InChI=1S/C26H42N2O2/c1-24(23-29)28-25(30)19-15-12-10-8-6-4-5-7-9-11-13-16-20-26(2,3)21-17-14-18-22-27/h4-5,8-11,16,20,24,29H,6-7,12-15,17-19,21,23H2,1-3H3,(H,28,30)/b5-4-,10-8-,11-9-,20-16-/t24-/m1/s1
  • Key:WZQHSBKOWZOASP-QLZKPENWSA-N
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O-1812 is an eicosanoid derivative related to anandamide that acts as a potent and highly selective agonist for the cannabinoid receptor CB1, with a Ki of 3.4 nM at CB1 and 3870 nM at CB2. Unlike most related compounds, O-1812 is metabolically stable against rapid breakdown by enzymes, and produces a cannabinoid-like discriminative effect in rats, which is similar but not identical to that produced by cannabinoid drugs of other chemical classes.

See also

References

  1. Di Marzo V, et al. (February 2001). "Highly selective CB1 cannabinoid receptor ligands and novel CB1/VR1 vanilloid receptor "hybrid" ligands". Biochemical and Biophysical Research Communications. 281 (2): 444–51. doi:10.1006/bbrc.2001.4354. PMID 11181068.
  2. Baskfield CY, Martin BR, Wiley JL (April 2004). "Differential effects of Δ-tetrahydrocannabinol and methanandamide in CB1 knockout and wild-type mice". The Journal of Pharmacology and Experimental Therapeutics. 309 (1): 86–91. doi:10.1124/jpet.103.055376. PMID 14718593. S2CID 36621393.
  3. Wiley JL, et al. (August 2004). "A comparison of the discriminative stimulus effects of Δ-tetrahydrocannabinol and O-1812, a potent and metabolically stable anandamide analog, in rats". Experimental and Clinical Psychopharmacology. 12 (3): 173–9. doi:10.1037/1064-1297.12.3.173. PMID 15301634.
  4. Wiley JL, Smith FL, Razdan RK, Dewey WL (March 2005). "Task specificity of cross-tolerance between Δ-tetrahydrocannabinol and anandamide analogs in mice". European Journal of Pharmacology. 510 (1–2): 59–68. doi:10.1016/j.ejphar.2005.01.006. PMID 15740725.
  5. Breivogel CS, et al. (July 2008). "Sensitivity to Δ-tetrahydrocannabinol is selectively enhanced in β-arrestin2 -/- mice". Behavioural Pharmacology. 19 (4): 298–307. doi:10.1097/FBP.0b013e328308f1e6. PMC 2751575. PMID 18622177.
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